Apple Watch not unlocking QMac since 9.1 and/or macOS 26.5.1

MontanaKarl

Until recently, I could open Quicken Mac reliably with my Apple Watch.

I'm not sure whether it was the update to QMac 9.1, or the update to macOS 26.5.1 - but not only do I almost never get prompted to unlock with my watch any longer…. QMac Settings > Security often doesn't even show the checkbox /text to "Allow Apple Watch to unlock this file".

Typical scenario… my Mac opens / unlocks with my Apple Watch. I launch Quicken, and am prompted for the password. Go to Quicken > Settings after typing in the password, and the Security only shows the 'encrypt' option.

Wait a few minutes, open Quicken Settings again - and now Quicken realizes that there is an Apple Watch authorized for the system and things are back to normal. Other times, Quicken never recognizes that system Watch setting and I have to restart the Mac. Never had any of these issues before.

Here's the normal System > Settings > Touch ID & Password setting:

And here is the Quicken Security tab after it finally recognizes my watch exists:

For those not familiar with it, here's the normal Quicken Launch pop-up that causes the watch haptics to click. Makes no sense that the Mac detects the watch and Quicken no longer does reliably.

Jon

@MontanaKarl I haven't had the Apple Watch unlock feature turned on for a while. I tried turning it on this afternoon to see if I could duplicate what you're seeing and it does appear to be unreliable as you describe, but for me it isn't just affecting Quicken. I can't even get it to reliably unlock my Mac when I wake it from sleep, most of the time it tries & fails and I have to fall back on either Touch ID or typing my password to get in to my Mac. So I'm inclined to think this is a Mac OS problem & not a Quicken problem.